Geordi went out with that Christy Henshaw woman for at least a month. Of course, that was only after John Doe magically gave him the confidence to ask her out. But yeah, Geordi loved the ladies. He was just terrible at interacting with them.
Harry always had success with the ladies. His ladies just always turned out to be holograms or disease-ridden aliens. Not his fault.
The hologram left him for Tuvok. He epically failed with the Dellany sisters... left his willing girlfriend in Ex Post Facto so he could be with Tom, bumbled every effort with Seven of Nine, was with the dead chick for awhile, was used by that elf terrorist, but yes... because of the alien chick on the community ship, Harry Kim has the sole distinction of being the only main cast member in the Trek franchise to get an STD. Did I miss anyone?
I was going to correct that, but I remember a scene between her and Tasha in "The Naked Now" where Tasha comes on pretty strong... all her 'I'm just trying on your clothes Deanna, do you think this dress makes me look pretty?' was just a prelude for a shower scene, I'm sure of it.
Or maybe he was a "holo-sexual." By the mid 24th century, there will be holo-sexuals right? People whose primary sexual congress will be with holodeck characters. The secretary in the Dixon Hill fantasy was nice looking.
I guess that would be Barclay's orientation. Don't tell me he didn't get it on with the Goddess of Empathy.
Perhaps Dixon Hill's secretary and the Goddess of Empathy get it on? When you walk out without shutting the holodeck down first, who knows what happens?